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17 Photos of Throwback Celebrities Who Are Old-School Cool

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A man with short dark hair and sideburns rests his head on his hand, wearing a ring and a collared shirt, looking directly at the camera with a neutral expression. The image is in black and white.
Terry Disney / Getty Images

There’s something magical about an old-school celebrity. The times of the past were just built different, and in some ways, before, maybe what we think of as “cool” back then was so much more unique and far less uniform than it can be now. I’m not sure. What I do know is that these photos of varying old-school celebrities certainly had people swooning left and right. It’s really no surprise, too.

1. Robert Redford

A man in a suit, striped tie, and fedora hat sits indoors. He has blonde hair and a serious expression. A blurred window view with an old car and building is in the background.
Michael Ochs Archives / Getty Images

2. Steve McQueen

A man in a white cowboy hat and striped shirt stands beside a truck with saddles and a sign reading “JR BONE.” He looks to the side with a serious expression.
FPG / Getty Images

3. Paul Newman

A man in sunglasses and a black racing jacket holds a drink can while talking to another man in a tan jacket indoors, with people and windows in the background.
Michael Ochs Archives / Getty Images

4. Alain Delon

A man in a suit and tie sits outdoors, holding a cigarette and looking at the camera with a slight smile. The photo is black and white and taken from above.
Evening Standard / Getty Images

5. Burt Reynolds

A man with short dark hair and sideburns rests his head on his hand, wearing a ring and a collared shirt, looking directly at the camera with a neutral expression. The image is in black and white.
Terry Disney / Getty Images

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6. Richard Roundtree

A man with an afro and mustache, wearing a leather jacket and turtleneck, sits on a couch and looks to the side with a serious expression. The background features wooden paneling.
Michael Ochs Archives / Getty Images

7. Bruce Lee

A man in traditional martial arts clothing sits on the floor indoors, resting his arms on his knees and looking to the side with a thoughtful expression.
Michael Ochs Archives / Getty Images

8. Jimi Hendrix

A Black man with an afro hairstyle passionately singing or playing guitar on stage, wearing a patterned shirt and a decorative scarf, shown in dramatic black and white lighting.
Evening Standard / Getty Images

9. David Bowie

Black and white photo of a person in a suit adjusting controls on a sound mixing board in a recording studio.
Michael Ochs Archives / Getty Images

10. Pam Grier

A woman with short curly hair gently holds a man’s neck with both hands as they stand close, gazing into each other’s eyes. The image is in black and white.
Michael Ochs Archives / Getty Images

11. Diana Ross

A smiling woman in a striped sweater holds a young child with bows in her hair while standing in a busy indoor public space with people in the background.
Dennis Stone / Getty Images

12. Jane Birkin

A woman sits cross-legged on a patterned rug in a cluttered room, resting her elbow on her knee and her head on her hand, gazing off thoughtfully. The space is filled with eclectic decor and personal items.
R. Viner / Getty Images

13. Catherine Deneuve

Black and white photo of a woman with voluminous, wavy hair looking slightly to the side. She has dramatic eye makeup and a soft expression. A lamp and part of a wall are visible in the blurred background.
Michael Ochs Archives / Getty Images

14. Raquel Welch

A woman in a pink dress with a unique neckline stands beside a man in a suit and glasses who is holding a black umbrella over her at a formal outdoor event.
Archive Photos/Getty Images

15. Faye Dunaway

A woman with light brown hair holds a Nikon film camera close to her face, focusing intently as she prepares to take a photograph.
Archive Photos / Getty Images

16. Lauren Hutton

A woman in a fur coat and elegant dress walks past a roped-off area, with people in yellow raincoats and others standing nearby on a wet sidewalk.
Michael Ochs Archives / Getty Images

17. Cher

A woman with long dark hair and bangs in profile wears a sparkling, one-shoulder dress against a dark background.
Michael Ochs Archives / Getty Images

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Meet the Writer


Matt Staff

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just easily he could be on the hunt for the next addition to his steadily growing plant family.



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